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Fluoroalkyl ether sulfonate surfactants

Inactive Publication Date: 2010-05-13
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0052]One of the advantages of using the surfactants comprising the fluoroalkyl ether sulfonate surfactant of the present invention in a dispersion polymerization processes is to achieve equally stable dispersions and increased polymerization rate while using reduced fluorine content. Further the reduced fluorine content of the surfactant increases the “fluorine efficiency”. By the term “fluorine efficiency” as used herein is meant the ability to use a minimum amount of fluorosurfactants and use a lower level of fluorine to obtain the desired dispersion of polymers.

Problems solved by technology

However, the fluorinated materials derived from longer perfluoroalkyl chains are more expensive.

Method used

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  • Fluoroalkyl ether sulfonate surfactants

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0103]C3F7OCF2CF2I (100 g, 0.24 mol) and benzoyl peroxide (3 g) were charged to a pressure vessel under nitrogen. A series of three vacuum / nitrogen gas sequences was then executed at −50° C. and ethylene (18 g, 0.64 mol) was introduced. The vessel was heated for 24 hour at 110° C. The autoclave was cooled to 0° C. and opened after degassing. Then the product was collected in a bottle. The product was distilled giving 80 g of C3F7OCF2CF2CH2CH2I in 80% yield. The boiling point was 56˜60° C. at 25 mm Hg (3333 Pa).

[0104]Potassium thiocynate (21.34 g, 0.22 mol) was added to the mixture of C3F7OCF2CF2CH2CH2I (50 g, 0.11 mol) and trioctylmethylammonium chloride (0.2222 g) in 50 g of water. The reaction was heated overnight at 90° C. After phase separation, the product C3F7OCF2CF2CH2CH2SCN was distilled as a colorless liquid (32 g, 78%). The compound can be characterized by: b.p. 83˜85 oC / 2.3 torr; 1H NMR (CDCl3, 400 MHz) δ 3.10˜3.07 (2H, m), 2.58˜2.46 (2H, m); 19F NMR (CDCl3, 373 Hz) δ−81....

example 2

[0109]C3F7OCF2CF2I (100 g, 0.24 mol) and benzoyl peroxide (3 g) were charged to a pressure vessel under nitrogen. A series of three vacuum / nitrogen gas sequences was then executed at −50° C. and ethylene (18 g, 0.64 mol) was introduced. The vessel was heated for 24 hour at 110° C. The autoclave was cooled to 0° C. and opened after degassing. Then the product was collected in a bottle. The product was distilled giving 80 g of C3F7OCF2CF2CH2CH2I in 80% yield. The boiling point was 56˜60° C. at 25 mm Hg (3333 Pa).

[0110]C3F7OCF2CF2CH2CH2I (220 g, 0.5 mol) was added to the mixture of ethanol (250 mL) and water (250 mL). Sodium sulfite (126 g, 1 mol) was added, followed by 15 g copper. The reaction mixture was stirred vigorously under reflux for a week. 500 mL water was added and filtered at 75° C. The filtrate was cooled and the product C3F7OCF2CF2CH2CH2SO3Na was collected by filtration as white solid (86 g, 41.35%). The compound was characterized by: 1H NMR (CDCl3, 400 MHz) δ 3.19˜3.15 ...

example 3

[0115]Following the general procedure of Comparative Example B, the Surfactant Solution used in Example 3 was made from 0.88 g of C3F7OCF2CF2CH2CH2SO3Na dissolved in 500 mL of deionized water. There was no additional water precharge. Results are reported in Table 5.

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Abstract

A compound of Formula (1)Rf—O—(CXX′)m—(CY2)nSO3M   (1)whereinRf is a C1 to C4 linear or branched perfluoroalkyl group,X and X′ are each independently H or F, provided that at least one of X or X′ is F,each Y is independently H or F,m is an integer from 1 to 4,n is an integer from 1 to 2, andM is H, NH4, Li, Na or K,provided that when CXX′ is CHF or CFH, then n is 2.

Description

FIELD OF THE INVENTION[0001]This invention relates to a process for the dispersion polymerization of a fluorinated olefin monomer in an aqueous polymerization medium in the presence of a fluoroalkyl ether sulfonate surfactant.BACKGROUND OF THE INVENTION[0002]Dispersion processes for polymerizing fluoro olefin monomers in aqueous media employ a surfactant to provide stability to the aqueous dispersion of particles of the resulting fluoropolymer. Different surfactants are chosen for use in dispersion polymerization because of their influence on reaction rate, dispersed fluoropolymer particle size, dispersion stability, color and the like.[0003]Fluorosurfactants used in the polymerization are usually anionic, non-telogenic, soluble in water and stable to reaction conditions. The fluorosurfactants as disclosed in U.S. Pat. No. 6,774,164 contain perfluoroalkyl groups having 4 to 18 carbon atoms. It is also known that the presence of a fluorocarbon “tail” in the hydrophobic segment of sur...

Claims

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Application Information

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IPC IPC(8): C08L81/08C07C309/04C09K3/00
CPCA61K8/466A61Q19/00C11D1/004C08F214/18C07C309/10C08F14/18C11D1/14
Inventor PENG, SHENGHUNG, MING-HONGJUNK, CHRISTOPHER P.TANG, PHAN LINH
Owner EI DU PONT DE NEMOURS & CO
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